| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H12O6 |
| Molecular Weight | 324.2843 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C(=O)C3=C(OC2=C4[C@@H]5C=CO[C@@H]5OC4=C1)C=CC=C3O
InChI
InChIKey=UTSVPXMQSFGQTM-DCXZOGHSSA-N
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
Sterigmatocystin is a mutagenic and carcinogenic mycotoxin initially produced by species of Aspergillus. Sterigmatocystin is a precursor of aflatoxin B1. In vitro, Sterigmatocystin activates ATM, p53, and Chk2 and damages DNA, inducing G2 phase cell cycle arrest; this mechanism may also involve PI3K/Akt/mTOR signaling. In vivo, chronic administration of sterigmatocystin decreases levels of glutathione, ascorbic acid, and α-tocopherol and increases levels of ROS, increasing lipid peroxidation.
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PubMed
Patents
Sample Use Guides
Rats: The incidence of chromosome aberrations in bone-marrow cells increased and reached the maximum level at 12 h after an intraperitoneal injection of 10(-1) mM(31.2 mg)/kg body weight of Sterigmatocystin and decreased gradually to the original level after 96 h.
Route of Administration:
Intraperitoneal
The human hepatoma cell line HepG2 a significant dose-dependent increase of DNA strand breaks was found after treatment with Sterigmatocystin (3 and 6 uM) respectively for 1 h. Increases in ROS level and the expression of 8-OHdG were also observed. A statistically significant increase in AO fluorescence intensity was observed in cells treated with Sterigmatocystin (1.5, 3 and 6 uM) for 1 h.
SUBSTANCE RECORD
